Potassium Phosphate, Tribasic → methyl 9-benzenesulfonyl-9H-[1,9']bicarbazolyl-1'-carboxylate

HRID 76376

Reaktionsgleichung

Reaktionsgleichung von HRID 76376
[C:1]1([C:14]([O:16][CH3:17])=[O:15])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:18]1([S:24]([N:27]2[C:39]3[C:38](Br)=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[C:18]1([S:24]([N:27]2[C:39]3[C:38]([N:12]4[C:13]5[C:1]([C:14]([O:16][CH3:17])=[O:15])=[CH:2][CH:3]=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)(=[O:25])=[O:26])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 643304methyl 9H-carbazole-1-carboxylateHCID 674051829-(Benzenesulfonyl)-1-bromocarbazole

Produkt 1

HCID 68243195methyl 9-benzenesulfonyl-9H-[1,9']bicarbazolyl-1'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

8.0 g (42.2 mmol) of copper(I) iodide, 11.7 ml (97.5 mmol) of trans-cyclo-hexanediamine are added to a well-stirred suspension of 26.3 g (117 mmol) of methyl 9H-carbazole-1-carboxylate, 45.2 g (117 mmol) of 9-benzenesulfonyl-1-bromo-9H-carbazole and 416.4 g (1961 mmol) of potassium phosphate in 1170 ml of dioxane, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol. Yield: 43 g (81 mmol), 70% of theory.

Aufarbeitung

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0c25fe28c9c74fb2ae1b964d5d9b0360
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835626B2

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